Triethylamine → 2-((Benzyloxy)methyl)-1,3-dioxane

HRID 31641

Reaction equation

HRID 31641 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12](O)[CH2:13][CH2:14][OH:15].C(OCC)(OCC)OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>>[CH2:1]([O:8][CH2:9][CH:10]1[O:15][CH2:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 104421,3-PropanediolHCID 31214Ethyl orthoformateHCID 108989(Phenylmethoxy)acetaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 597923782-((Benzyloxy)methyl)-1,3-dioxaneYield 58%

Procedure

A mixture of benzyloxyacetaldehyde (3.6 g, 24 mmol), 1,3-propanediol (5.2 ml, 72 mmol), triethyl orthoformate (4 ml, 24 mmol), and p-toluenesulfonic acid monohydrate (414 mg, 2.45 mmol) was stirred at room temperature for 17 hours. To the reaction mixture, triethylamine (669 μl, 4.8 mmol) was added, which was concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate) to obtain the title compound (2.9 g, yield: 58%) as a light yellow oil.

Workup

  1. concentrationwhich was concentrated
  2. customThe residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate)

Sources & evidence

ORD record
ord-9f39e15806ee44feb5cf00cee9492e0e
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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